Bennett and his wife, Mary Elayne "Elayne" Glover, have two sons, John and Joseph. Elayne is the president and founder of Best Friends Foundation, a national program promoting sexual abstinence among adolescents. He is the younger brother of Washington attorney Robert S. Bennett.

Bennett tends to take a conservative position on affirmative action, school vouchers, curriculum reform, and religion in education. As Education Secretary, he asked colleges to better enforce drug laws and supported a classical education. He frequently criticized schools for low standards. In 1988 he called the Chicago public school system "the worst in the nation."[7] He coined the term "the blob" to describe the state education bureaucracy,[8] a term which was later taken up in Britain by Michael Gove.[9]

Bennett is a staunch supporter of the War on Drugs and has been criticized for his views on the issue. On Larry King Live, he said that a viewer's suggestion of beheading drug dealers would be "morally plausible."[10] He also "lamented that we still grant them [drug dealers] habeas corpus rights."[11]

Bennett began hosting Morning in America, a nationally syndicated radio program produced and distributed by Salem Communications, in 2004.[13] The show aired live weekdays from 6 to 9 a.m. Eastern Time, and was one of the only syndicated conservative talk shows in the morning drive time slot. However, its clearances were limited due to a preference for local shows in this slot, and the show got most of its clearances on Salem-owned outlets. Morning in America was also carried on Sirius Satellite Radio, on Channel 144, also known as the Patriot Channel[14] Bennett retired from full-time radio on March 31, 2016.[15] In 2017, Bennett launched a podcast, The Bill Bennett Show.[16]

In 2008, Bennett became the host of a CNN weekly talk show, Beyond the Politics. The show did not have a long run, but Bennett remained a CNN contributor until he was let go in 2013 by then-new CNN president, Jeff Zucker.

In 2003, it became publicly known that Bennett was a high-stakes gambler who lost millions of dollars in Las Vegas.[17] Criticism increased in the wake of Bennett's publication, The Book of Virtues, a compilation of moral stories about courage, responsibility, friendship and other examples of virtue. Joshua Green of the Washington Monthly said that Bennett failed to denounce gambling because of his own tendency to gamble. However, Bennett and Empower America, the organization he co-founded and headed at the time, opposed an extension of casino gambling in the United States.[18]

Bennett said that his habit had not put himself or his family in any financial jeopardy. After Bennett's gambling problem became public, he said he did not believe his habit set a good example, that he had "done too much gambling" over the years, and his "gambling days are over". "We are financially solvent," his wife Elayne told USA Today. "All our bills are paid." She added that his gambling days are over. "He's never going again," she said.[19]

Several months later, Bennett qualified his position, saying "So, in this case, the excessive gambling is over." He explained "Since there will be people doing the micrometer on me, I just want to be clear: I do want to be able to bet the Buffalo Bills in the Super Bowl."[20]

On September 28, 2005, in a discussion on Bennett's Morning in America radio show, a caller to the show proposed that "lost revenue from the people who have been aborted in the last 30 years" could preserve Social Security if abortion wasn't permitted following Roe v. Wade. Bennett responded that aborting all African-American babies "If you wanted to reduce crime, you could—if that were the sole purpose—you could abort every black baby in this country and the crime rate would go down. That would be an impossible, ridiculous, and morally reprehensible thing to do, but your crime rate would go down."[21]

Bennett responded to the criticism saying, in part:

A thought experiment about public policy, on national radio, should not have received the condemnations it has. Anyone paying attention to this debate should be offended by those who have selectively quoted me, distorted my meaning, and taken out of context the dialogue I engaged in this week. Such distortions from 'leaders' of organizations and parties is a disgrace not only to the organizations and institutions they serve, but to the First Amendment.[22]